HCID 68866442, compound → HCID 11573782, compound

HRID 1725942Notes

Reaction equation

HRID 1725942 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:23]=[CH:22][C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[C:15]=1[C:24]([OH:26])=[O:25])(=[O:12])=[O:11])([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:23]=[CH:22][C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[C:15]=1[C:24]([OH:26])=[O:25])(=[O:12])=[O:11]

Participants

4

Reactant 1

HCID 68866442HCID 68866442, compound

Product 1

HCID 11573782HCID 11573782, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 270 (1.4192 g, 3.77 mmol) in methanol (20 mL) was added to Raney-nickel (14.1 g). The vessel was pressurized to 60 psi with H2 and shaken for 5 hours. The reaction was then filtered and concentrated to yield the desired product (1.18 g, 90%). MS (ESI(+)) m/e 332 (M+H)+, 364 (M+NH4)+, 369 (M+Na)+; MS (ESI(−)) m/e 345 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.48 (d, 1H), 7.17 (t, 1H), 6.92 (d, 1H), 6.80 (d, 1H), 6.71 (d, 3H), 6.52 (t, 1H), 2.92 (m, 2H), 2.58 (m, 2H), 1.60 (m, 4H).

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-998b3b3ac5e94439b813963d260b6e07
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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